Newbie and petrified of towing TT

First of all I want to commend you for taking this challenge and not letting the fear keep you from doing what you want. You are half way there. I would suggest that you take it out and go to a parking lot with someone experienced with towing who is willing to ride a long with you for basically a training run. Thirty foot sounds like a long unit for a first time pull but we've owned a 19', a 22', a 25, a 32' and now a 35' and DH says that the longer they are, the easier to back. I've towed all three with him with me coaching me and to this day, when turning he reminds me to take it wide. That's what you need - a tutor. You can do it! As for the generator - you'll need at list something like a Honda 3000, or 3500 watt to handle AC. Of course, if you camp in cooler weather, you won't need it and if you have hookups.